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Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities

Based on 1,2-dimethoxyphenyl (veratrole, open) and 1,2-methylenedioxyphenyl (pepper ring, close)-derived pyridine–triazole analogues, two groups of copper(ii) complexes, namely, Group I(C1–C3) and Group II(C4–C6) were synthesized and fully characterized. All ligands and complexes were tested in vitr...

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Autores principales: Hong, ZhaoGuo, Zheng, Chu, Luo, Bi, You, Xin, Bian, HeDong, Liang, Hong, Chen, ZhenFeng, Huang, FuPing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9049676/
https://www.ncbi.nlm.nih.gov/pubmed/35496028
http://dx.doi.org/10.1039/c9ra10677d
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author Hong, ZhaoGuo
Zheng, Chu
Luo, Bi
You, Xin
Bian, HeDong
Liang, Hong
Chen, ZhenFeng
Huang, FuPing
author_facet Hong, ZhaoGuo
Zheng, Chu
Luo, Bi
You, Xin
Bian, HeDong
Liang, Hong
Chen, ZhenFeng
Huang, FuPing
author_sort Hong, ZhaoGuo
collection PubMed
description Based on 1,2-dimethoxyphenyl (veratrole, open) and 1,2-methylenedioxyphenyl (pepper ring, close)-derived pyridine–triazole analogues, two groups of copper(ii) complexes, namely, Group I(C1–C3) and Group II(C4–C6) were synthesized and fully characterized. All ligands and complexes were tested in vitro by MTT assays on seven tumour cell lines (T24, Hep-G2, Sk-Ov-3, MGC-803, HeLa, A549 and NCI-H460) and one normal liver cell line (HL-7702). Surprisingly, the pepper-ring-derived complexes (C4–C6) showed significantly enhanced cytotoxicity compared with the 1,2-bimethoxyphenyl ring-derived complexes (C1–C3) and the standard anticancer drug cisplatin. Cellular uptake assays indicated that the Cu accumulation was consistent with cytotoxicity. In addition, flow cytometry and western blot analysis showed that the apoptosis of the leading complex C4 may be induced by the Bcl-2 family-mediated proteins through the mitochondrial dysfunction pathway. Furthermore, UV-vis and fluorescence spectroscopy assays revealed that C4 has stronger insertion-binding interactions with CT-DNA than C1 and the fluorescence of C1 and C4 with BSA is mainly quenched by static quenching.
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spelling pubmed-90496762022-04-29 Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities Hong, ZhaoGuo Zheng, Chu Luo, Bi You, Xin Bian, HeDong Liang, Hong Chen, ZhenFeng Huang, FuPing RSC Adv Chemistry Based on 1,2-dimethoxyphenyl (veratrole, open) and 1,2-methylenedioxyphenyl (pepper ring, close)-derived pyridine–triazole analogues, two groups of copper(ii) complexes, namely, Group I(C1–C3) and Group II(C4–C6) were synthesized and fully characterized. All ligands and complexes were tested in vitro by MTT assays on seven tumour cell lines (T24, Hep-G2, Sk-Ov-3, MGC-803, HeLa, A549 and NCI-H460) and one normal liver cell line (HL-7702). Surprisingly, the pepper-ring-derived complexes (C4–C6) showed significantly enhanced cytotoxicity compared with the 1,2-bimethoxyphenyl ring-derived complexes (C1–C3) and the standard anticancer drug cisplatin. Cellular uptake assays indicated that the Cu accumulation was consistent with cytotoxicity. In addition, flow cytometry and western blot analysis showed that the apoptosis of the leading complex C4 may be induced by the Bcl-2 family-mediated proteins through the mitochondrial dysfunction pathway. Furthermore, UV-vis and fluorescence spectroscopy assays revealed that C4 has stronger insertion-binding interactions with CT-DNA than C1 and the fluorescence of C1 and C4 with BSA is mainly quenched by static quenching. The Royal Society of Chemistry 2020-02-11 /pmc/articles/PMC9049676/ /pubmed/35496028 http://dx.doi.org/10.1039/c9ra10677d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Hong, ZhaoGuo
Zheng, Chu
Luo, Bi
You, Xin
Bian, HeDong
Liang, Hong
Chen, ZhenFeng
Huang, FuPing
Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title_full Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title_fullStr Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title_full_unstemmed Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title_short Two groups of copper(II) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
title_sort two groups of copper(ii) pyridine–triazole complexes with “open or close” pepper rings and their in vitro antitumor activities
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9049676/
https://www.ncbi.nlm.nih.gov/pubmed/35496028
http://dx.doi.org/10.1039/c9ra10677d
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